Little Big Maid
by Winterwolke
Summary: Sometimes Sam gets kinky. When he saw the maid dress on the internet, he knew a new game was on. Dean isn't so sure if he likes his "present". Maid!Dean, Bottom!Dean, Top!Sam


A/N: Very much heartfelt thanks to my beta reader Harini, who did exceptional work (as always) and who beta'd this story in less than a day. It isn't her fault it took me six month to gather the courage to look at it again. It's the first smut-story I've ever written and I'm very anxious about it. It would be nice if you'd tell me what you think. 

The thing about changes is that they can be good or bad. A changed recipe can bring so much more spice to your taste buds or it can be a horrible disaster. Some changes improve the quality of your life or make it so much worse. And it's a thing of perception. What's good for another might be bad for you.

It's the same with changing clothes and Dean is currently experiencing the bad side of change. He can't decide what's worse - the itchy but definitely sexy and ridiculously too short dress or the ridiculous but definitely thrilling barely-there stockings. Hell, even the pink feather duster sitting on his bedside table has something so naughty his belly is not only tightening in discomfort but slight excitement. Still he wishes he could be somewhere else - or wear something else at least. 

When Sam entered his bedroom this morning, holding a tiny maid dress with a crisp white apron, a delicate white bonnet and black stockings, Dean knew things were about to change. Just now and then Sam likes to freshen things up between them. And he was a kinky son of a bitch. Hence the maid dress. The game was on as soon as Dean's orders were clear. He showered, shaved everything (and that was embarrassing enough, he never had to do that before) and then put on the dress.

It's a nightmare. The black skirt ends in white ruffles that touch all the right places, especially since Sam has forbidden any kind of underwear. It's a nice feeling and has his cock twitching for about 10 seconds before he's aware of the fact that if he stands upright the dress reveals his bare ass and, more horribly, his junk. It's just on the wrong side of short and Dean is fairly sure Sam knows. Really, it's the reason why he bought the dress in the first place. Sam knows Dean is a slut but he can't stand the idea of walking around half naked. He has no choice though, because Sam has set up a tight schedule. After dressing he has to make breakfast - pancakes, coffee, fruit salad. It takes Dean very long to talk himself into leaving his bedroom. The Bunker is empty, safe for the both of them, but there is a minor chance that one of their friends will show up and then it will be more than awkward. It's one thing to accept that he and Sam are more than just brothers and haven't been for a long while but it's a whole other thing for someone to get caught in the middle of one of their games. At least he doesn't have to wear heels while being dressed like that.

Dean makes his way through the narrow halls of the Bunker and although nobody sees him (he's fairly sure Sam is watching somehow, but that's okay, this show is for Sam after all), his cheeks are flushed in a mix of humiliation and arousal. After the initial shock of being half-naked he feels all the subtle ways the dress clings to all the right places. By the time he enters the kitchen he's half hard, his cock constantly caressed by the soft but firm ruffles, the lace of his stockings rubbing his thighs, the tulle of the too-tight top scratching his nipples just right. His breathing has increased and he wishes he'd been allowed to touch himself. Just a little bit to take the edge of. It's ridiculous how he's so turned on just wearing a maid dress but he is and he's ready for more. Sam has planned something amazing and waiting for it makes half the fun. Still Dean can't resist a little treat - he's proud he left his bedroom at all - and he steps to the counter where he wants to prepare Sam's breakfast. He steps close, presses his groin against the front and rubs himself at the sturdy surface. Dean can't keep in the moan as he feels the friction but immediately knows he made a mistake when his cock hardens further and now he's not only embarrassed but frustrated. He knows he can't get off because Sam was very clear with his instructions and threatened to punish him if he disobeys. Also his painful erection makes it hard to work on the counter: He bumps against it with every move, preventing him from concentrating on the task at hand which isn't good. Sam will punish him even more if breakfast is late. The dress is impractical and Dean has to try hard not to dirty the white apron. Another instruction, of course, but he would have tried anyway. With the dress comes a strange feeling of perfection. This maid dress really is a cliche but it helps Dean feel in character: Sam is some very important, rich guy who needs his household in perfect shape, perfectly clean and organized. And Sam needs his staff the same way. Dean wants to please him. Sam once said that one of Dean's best characteristics is his ability to devote himself to a situation. That makes their little games so much more intense. It's the same now. He still feels awkward wearing next to nothing but he's also a maid now and he wants to be good, so good.

Dean's so absorbed by his task that he doesn't notice he isn't alone anymore. Sam comes into the kitchen, wearing one of those dead-guy-robes and pajama bottoms. He steps behind Dean, not close enough to touch but definitely into his personal space and gruffs out a rough "Good Morning". Dean nearly jumps out of his skin and promptly lets go of the flour bag. It's not much but enough to mess up the counter - and to put some stains on the apron. Dean whirls around, more embarrassed than he likes to admit, and makes an awkward and shaky curtsey as he says the instructed words "Good Morning, Sir." 

Sam takes a step back to admire his work. When he saw the dress weeks ago on the internet he knew he had to make Dean wear it. It looked perfect for his brother in his imagination and it definitely looks even better in reality. The skirt is too short, naturally, and exposes a broad stripe of skin and Dean's still erect dick. The white ruffles and the black lace of the stockings are the perfect frame for something so gorgeous and delicious as his brother's cock and Sam unconsciously licks his lips at the sight. His gaze goes higher, takes in the formerly clean white apron before he takes in the too tight top, spanning over Dean's chiseled pecs, the broad shoulders, his flat stomach. The last thing is the little bonnet on his head. Dean really gave his all while he slipped into his role. It's cute and sexy and exciting and Sam's dick twitches with interest. And it has every reason to do so, because Dean just broke one of the rules: not getting the apron dirty. And rubbing his dick all over the front of the counter. That isn't forbidden per se but Sam saw it and he wants to make sure Dean obeys the rules. It's a good opportunity to make an example and it promises so much fun. He takes in Dean's stance, his lowered eyes, his obediently folded hands in front of him. It makes Sam smile. Dean's fully into this game, even if he still struggles with the dress code or itches to look up at Sam to see what he thinks.

Sam decides to take it slow. The day he has planned is long and it would be a shame if it ended too soon. He steps back into Dean's personal space and brings up his hand to lift Dean's chin to look him in the eyes. He basks in their soft glow, the color seeming to change depending on his brother's current mood. And if Sam had a doubt if Dean was into the game he hasn't one now. His eyes are sparkling green, the color of jade and his pupils are dilated. Not as much as they are when they have mind-numbing, earthquaking sex but they will go there soon. His lips are swollen like he's licked them too much, a tell that he is nervous, but excited. Sam leans down to run his tongue over said lips, pink and plush and soft and he hears Dean sigh. However, it's not the moan he's heard when Dean rubbed himself on the furniture and it's not good enough. Sam deepens the kiss, presses demandingly against Dean and his brother opens up immediately, lets Sam in and starts a heated battle. His hand grabs the spiky hair, cautious of the bonnet, tilting Dean's head back to get a better angle for his venture. It draws the sweetest moans from his brother and finally Sam's tongue wins the duel and he gets to explore his prize. After a long minute they break away, panting heavily. He feels Dean suck in a deep breath, sucks in the oxygen Dean exhales and it's exhilarating how close they are, that they let themselves have this. Then the moment is over. Dean's erection is poking his thigh and his brother wriggles because he wants more, always more. Sam's about to give him exactly what he wants - what Sam wants that is. And Sam wants to make him squirm, desperate for his cock and desperate to come.

"Look what we have here. Didn't I tell you that you were to keep your clothes clean? I can't accept my staff walking around in dirty clothes like tramps. What do you have to say for yourself?"

His voice is strict and Sam's amazed he manages without breaking character. Dean's just too adorable in his dress, trying to hide his uneasiness. Still he plays his role and answers "Nothing, Sir, I'm sorry I dirtied my apron. Will you forgive me, Sir?" His voice is a little shaky but Sam's sure it's hidden anticipation. Dean wants this as much as he does.

"I will, after I punish you. I gave you a fair warning about what would happen if you disobeyed my orders. Turn around now and receive your punishment." And his brother does. He turns around, lays his hands flat on the counter, bends forward and pushes his ass out. The frilly skirt ends midway down his ass but Sam pulls it up anyway. He takes in the sight, the perfect globes he likes to caress, to knead, to lick and bite. Now though, he will paint them red and his cock is rock hard with merely the thought.

"I will give you 25 slaps for your disobedience and you will get punished more for rubbing yourself on the counter front. You are here to cook and clean, not to dirty my property because you are a horny slut. Are we clear?"

Dean's breath hitches in excitement and he wriggles his ass in a delicious way before he answers "Yes, Sir".

"Good, stand still now." 

The first slap hits Dean's left cheek and he can't keep in a moan. Sam hasn't slapped him with full force but it's enough for it to sting. Dean's sure that patch of skin will color in a nice shade of pink but he hasn't time to dwell on it. The next hit comes immediately - on his right cheek - followed by a quick succession on either side before Sam stops and takes his time to stroke the reddened flesh. The hand doesn't stay at his ass, slips around to grab his hard cock. Dean can't control the sudden moan or the movement of his hips even if he wanted. Sam teases him mercilessly, his hand moving up and down his length in a firm grip, squeezing in all the right places. When his thumb slides over his sensitive crown Dean can't suppress a whimper. He feels his brother smirk as the hand leaves his aching cock and gets back to his original task. Sure enough the next series of slaps comes quickly and Dean feels the heat in his ass. His skin feels tender. Not so tender he won't be able to sit, but he will feel his punishment for a while, clearly what Sam intended. Again his brother stops, his hand slipping between the deeply flushed cheeks to tease the already quivering pucker. Sam lets his index finger circle around the hole, occasionally dipping into it. Dean pushes against the tormenting digit though Sam's never giving him enough to satisfy the need for more more more. 

It's mesmerizing how Dean wriggles and shakes, tries to bend back against Sam's probing finger and simultaneously pushing against the counter for friction. It isn't possible for how he stands but Sam finds it adorable nevertheless. And he feels the rising need building up in his own pants. He's hard enough to pound nails and he ponders for a moment what to do. They could have sex now but they're both not so young anymore and will need time for recovery. He goes over his plan for the day - can they have a quickie before breakfast and still do all the stuff Sam wants to do? His libido screams 'YES!' at him and finally he's willing to give in. His left hand that has been resting on the small of Dean's back, holding the skirt up, snakes around, up Dean's body, rubbing the tulle over one hardened nipple, waiting for a deep moan he knows this action will provoke. When it comes his hand wanders up until his fingers press against Dean's mouth. "Open up," he orders and is pleased when his brother follows the order immediately. Sam strokes the inside of his mouth while Dean licks and sucks on his fingers until they are thoroughly wet, then pulls them away with an audible pop that goes straight to his cock. Sometimes it's the small things that drive Sam crazy with lust. He then switches hands, brings the moist digits to the waiting hole and pushes in, two at once. Dean's still open from last night and it's more of an overture than necessity. His brother immediately fucks himself on the fingers, moans like a porn star but Sam learned long time ago that that's just Dean. He's always vocal, moaning, whimpering but in contrast to his everyday life he never talks during sex. Only when Sam demands it or he's desperate enough to beg. He never says "More, harder, faster" but his body speaks those words for him and Sam always knows what to do. He knows that Dean is desperate for his cock and he himself doesn't want to wait anymore. He tugs down his pajama pants, pulls his hand away and begins to rub up and down the crease, spreading his precome around. Then he lines up and finally pushes inside. 

The feeling of Sam inside of him is always magical in a way. Dean never feels as close to his brother as in those moments, when they are joined so tight that not even a sheet of paper would fit between them. It's only in bed that Dean can show his brother how deep he loves him, show his devotion, express his wish to never let Sam go. Even when things get kinky there's always love and safety. Even when Sam gets rough like now - he's picked up the spanking again, apparently some slaps were missing - he knows his little brother would never hurt him. Sex is Dean's way to tell Sam everything he can't put into words. 

Sam gives him a minute to adjust to the fullness inside of him, thoughtfully so because they aren't using lube. It's not strictly necessary, they had much fun together these last days and Sam is leaking so much. It's an exquisite torture to wait for Sam to move and Dean can barely hold in his pleas when his brother finally begins to do so. Very slowly though and very deliberately. More torture and Dean squirms, urges him on to go faster, harder. He pushes back, tries to take Sam deeper and whimpers when he hits that sweet spot inside of him that turns him into a puddle of sexual satisfaction. His moans grow louder and louder when suddenly his breath hitches. Sam's hand has sneaked up to his cock and grips it firmly, strokes it in time with the hard thrusts, gentles when he gentles, speeds up when he does. But every time Dean gets close to release the hand grabs the base of his cock, staves off the impending orgasm. He doesn't know how Sam does it, but his stamina is incredible and they are at it for several minutes already. His brother is always patient up to a certain point before he explodes and, Dean muses, it's the same with sex. His brother is a master of drawing things out, a master of teasing but when he's done with playing he explodes with a force that takes Dean's breath away. It's a fine line between excitement and fear because it's equally thrilling, frightening and beautiful to see Sam set loose, to see him free of worries and sorrow, even just for a moment or two. As Sam continues to drive him towards the edge and back again Dean can only hang on for the ride, lust once more taking over his thoughts.

Even after a couple of days spent lazy in their bedroom Dean's still tight and it slowly drives Sam crazy. Everything about Dean is perfect, starting with the color of his hair (in the artificial light of the Bunker it's a light brown but in the sunlight nearly golden), to his freckles (he even has some of them on his ass and Sam always wonders how they got there), to his muscular body (he'd eat fast food only if Sam wouldn't insist on salad sometime and how does he even manage to stay in shape?), to his well endowed cock (and it shouldn't be so thrilling to think about his brother's cock in the first place), to his tight channel that squeezes Sam just in the right places. It's hard to last when it's wet and hot and just the right side of friction without the lube and he has to keep himself occupied to not shoot his load right away. He distracts himself by going over today's plan, because he has to admit that he will never be able to pull off the whole 'maid thing'. Dean's just too delicious, too much of a walking temptation. Sam wanted to make him prepare breakfast, make Dean kneel on the table, use him as a holder for his newspaper while drinking his coffee, enjoying the view of his bare ass framed by the frisky dress. Then he wanted Dean to clean some shelves in some office just to see him bend and stretch while the dress shows everything. He wanted to throw Dean over some couch or table and fuck him after a long time of teasing before he takes him to his bedroom and ties him down, a neat package of pleasure. That goes all out of the window because Sam can't even take an hour looking at Dean in his costume. He wanted his brother to be desperate to be fucked, wanted to tease the hell out of him but in the end it's Sam who just can't last any longer. Dean is just heaven on earth and the opportunity is too good to let it pass.

Sam grips his brother by the hips as his thrusts speed up, sets a fast rhythm before he reaches around to give the same pleasure he feels. Dean is leaking like crazy and he uses the precome to make it easier. He thumbs the slip, spreads the wetness all over the hard member and jacks Dean off in time with his thrusts. Sam feels his brother's orgasm building and takes counter-measures. He hears the frustrated huff, hears it change to a needy moan as he hits the sweet spot and then repeats his actions a few times until Dean is so desperate he begins to beg. That's his goal, make Dean talk. The silence during sex is somehow unnerving. Sam knows it's because although Dean's a master at sex, has enough experience for three lives, his brother is eerily self-conscious when they are together. It's an extension of Dean's normal quirks and sometimes, to Sam's irritation, he brings them into bed. Sam wishes his brother could let go and he does in fact, but only under the right circumstances.

In the early days of their relationship the roles had been reversed; Dean on top, Sam being the one to be fucked. He liked it very, very much but soon realized Dean's head was not fully in the game. It took him a long time to recognize what was wrong and even longer to convince Dean to try something new. When Dean first noticed that he could let go of everything completely when he lets Sam take the lead and 'guide' him that was the first time either of them fully enjoyed themselves. The sex before had been good, no questions asked, but it got incredible when they changed roles. They switch now and then but Sam always stays in charge, no matter who does the fucking. It's just something Dean needs. He needs to give up control and responsibility for a little while so he can keep going when it matters. It was a hard transition for both of them but after years both of them know their place. Still Sam never adjusted to the silence and he likes to keep going until Dean can't do anything else but beg for release. And Sam likes his voice when he's reached this point. It's wrecked, rough but always needy and it's a such a huge turn on that Sam always has to finish soon after Dean breaks. This time is no exception.

As soon as Dean huskily says "Please, Sammy, let me finish, please," Sam speeds up, changes the angle slightly to hit his brother's prostate better, harder and Dean whimpers and moans shamelessly, too far gone to care anymore. Sam's hand still matches his pace, twists his grip with every up stroke until Dean comes with a choked of cry of "Sam!". He milks every last drop of come from his brother, wants Dean to enjoy the moment without distracting him by his movements. Dean shudders, goose bumps everywhere, a sure sign he really enjoyed what Sam does to him. When the last spurt of come is gone, Sam changes the angle again and needs only three more thrusts before he comes himself, a matching cry of "Dean!" on his lips while he fills the tight channel with his come. They're both panting heavily and finally Sam pulls out. He reaches for the paper towels to clean them up because Dean isn't able to function yet. They both sit down for a moment, leaning against the kitchen counter, catching their breaths. The maid dress is rumpled and somehow they managed to dislodge the bonnet though Sam has no idea how. One stocking is still in place, the other one pools around Dean's ankle. The offensive apron, the object of punishment, is now not only stained by flour but also by Dean's come. Sam's dick twitches as he thinks that this is a new reason for punishment but he's spent at the moment. The sex was exhausting but in a good way. In a few minutes they will be ready to continue their game. Sam looks at Dean, a sated smile in his handsome face and he leans over for a kiss, nothing fancy but an expression of love. 

Dean is beat. It might be just sex, but it was awesome sex nevertheless. He feels sated and pleasantly tired though they got up merely hours ago. He looks over to Sam, takes in the expression of utter bliss and ponders what to do next when his brother leans over to kiss him. It's a tender kiss, not really sexual, but a declaration of love and devotion. It's lazy and slow and Dean can't help but smile afterwards. They let themselves have a few minutes of sweet idleness at the kitchen floor before Sam heaves himself up and helps Dean get up as well. There is a smirk on Sam's face as he rakes his gaze over Dean's rumpled appearance but his voice is serious as he asks "Do you want to continue our game or do you want to go change?"

He thinks about the offer, about how he wants to explore what Sam has planned for today but he's still beat and on the wrong side of thirty. He leans over to kiss Sam once more before he answers "I'd like to change. But we can have fun with the dress again. I think there is a shelf that needs to be dusted somewhere around." He winks at his brother before he retreats to his bedroom, leaving Sam with a messy counter and some ideas for a resumption of their game.


End file.
